NO331321B1 - Fremgangsmate for fremstilling av lyofilisater med forbedret opplosningshastighet, lyofilisater med forbedret opplosningshastighet og rekondisjonerbarhet, samt farmasoytiske preparater som inneholder lyofilisatene - Google Patents
Fremgangsmate for fremstilling av lyofilisater med forbedret opplosningshastighet, lyofilisater med forbedret opplosningshastighet og rekondisjonerbarhet, samt farmasoytiske preparater som inneholder lyofilisatene Download PDFInfo
- Publication number
- NO331321B1 NO331321B1 NO20013703A NO20013703A NO331321B1 NO 331321 B1 NO331321 B1 NO 331321B1 NO 20013703 A NO20013703 A NO 20013703A NO 20013703 A NO20013703 A NO 20013703A NO 331321 B1 NO331321 B1 NO 331321B1
- Authority
- NO
- Norway
- Prior art keywords
- lyophilisates
- lyophilisate
- compound
- freeze
- filled
- Prior art date
Links
- 238000004090 dissolution Methods 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 238000004108 freeze drying Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000007710 freezing Methods 0.000 claims description 9
- 230000008014 freezing Effects 0.000 claims description 9
- -1 compound 2-methyl-5-methylsulfonyl-4-(1-pyrrolyl)-benzoylguanidine methanesulfonate Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- OURUCFSGKCZIPX-UHFFFAOYSA-N carbamimidoyl-[2-methyl-4,5-bis(methylsulfonyl)benzoyl]azanium;chloride Chemical compound Cl.CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(=O)NC(N)=N OURUCFSGKCZIPX-UHFFFAOYSA-N 0.000 claims 1
- FNDLQABGYJQJPH-UHFFFAOYSA-N n-(diaminomethylidene)-3-methylsulfonyl-4-propan-2-ylbenzamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC(C)C1=CC=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O FNDLQABGYJQJPH-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 15
- 239000003814 drug Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 108010083687 Ion Pumps Proteins 0.000 description 2
- 210000004413 cardiac myocyte Anatomy 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 210000004165 myocardium Anatomy 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012859 sterile filling Methods 0.000 description 2
- 238000011146 sterile filtration Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229960003408 cefazolin sodium Drugs 0.000 description 1
- FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- UADMBZFZZOBWBB-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-pyrrol-1-ylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(N2C=CC=C2)=C1S(C)(=O)=O UADMBZFZZOBWBB-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F26—DRYING
- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
- F26B5/00—Drying solid materials or objects by processes not involving the application of heat
- F26B5/04—Drying solid materials or objects by processes not involving the application of heat by evaporation or sublimation of moisture under reduced pressure, e.g. in a vacuum
- F26B5/06—Drying solid materials or objects by processes not involving the application of heat by evaporation or sublimation of moisture under reduced pressure, e.g. in a vacuum the process involving freezing
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/402—1-aryl substituted, e.g. piretanide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Molecular Biology (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Waveguide Aerials (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Medical Preparation Storing Or Oral Administration Devices (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19903275A DE19903275A1 (de) | 1999-01-28 | 1999-01-28 | Lyophilisate mit verbesserter Rekonstituierbarkeit |
| PCT/EP2000/000569 WO2000044354A1 (de) | 1999-01-28 | 2000-01-26 | Lyophilisate mit verbesserter rekonstituierbarkeit |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20013703D0 NO20013703D0 (no) | 2001-07-27 |
| NO20013703L NO20013703L (no) | 2001-07-27 |
| NO331321B1 true NO331321B1 (no) | 2011-11-21 |
Family
ID=7895601
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20013703A NO331321B1 (no) | 1999-01-28 | 2001-07-27 | Fremgangsmate for fremstilling av lyofilisater med forbedret opplosningshastighet, lyofilisater med forbedret opplosningshastighet og rekondisjonerbarhet, samt farmasoytiske preparater som inneholder lyofilisatene |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6770678B1 (ko) |
| EP (1) | EP1146863B1 (ko) |
| JP (2) | JP4562288B2 (ko) |
| KR (1) | KR20010108136A (ko) |
| AT (1) | ATE266387T1 (ko) |
| AU (1) | AU757781B2 (ko) |
| BR (1) | BRPI0007714B8 (ko) |
| CA (1) | CA2361237C (ko) |
| CZ (1) | CZ20012693A3 (ko) |
| DE (2) | DE19903275A1 (ko) |
| DK (1) | DK1146863T3 (ko) |
| ES (1) | ES2220404T3 (ko) |
| HU (1) | HU226585B1 (ko) |
| NO (1) | NO331321B1 (ko) |
| PL (1) | PL351140A1 (ko) |
| PT (1) | PT1146863E (ko) |
| RU (1) | RU2225709C2 (ko) |
| SK (1) | SK10542001A3 (ko) |
| UA (1) | UA70351C2 (ko) |
| WO (1) | WO2000044354A1 (ko) |
| ZA (1) | ZA200107081B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2664189T3 (es) | 2002-01-09 | 2018-04-18 | Emisphere Technologies, Inc. | Polimorfos de 4-(4-cloro-2-hidroxibenzoil)aminobutanoato de sodio |
| DE102004045825A1 (de) * | 2004-09-22 | 2006-03-23 | Merck Patent Gmbh | Lyophilisat enthaltend N-Diaminomethylen-2-methyl-4,5-di-(methylsulfonyl)-benzamid |
| US8158152B2 (en) * | 2005-11-18 | 2012-04-17 | Scidose Llc | Lyophilization process and products obtained thereby |
| EP2271327B1 (en) | 2008-05-09 | 2015-05-20 | Merck Patent GmbH | Pharmaceutical composition comprising rimeporide for treating diseases associated with beta-cell dysfunction |
| WO2009152168A2 (en) * | 2008-06-09 | 2009-12-17 | Awd. Pharma Gmbh & Co. Kg | Carboxylic acid salts of 2-amino-3-carbethoxyamino-6-(4-fluoro-benzylamino)-pyridine |
| US7795263B2 (en) * | 2008-07-08 | 2010-09-14 | Wildlife Laboratories, Inc. | Pharmaceutical combination for and method of anesthetizing and immobilizing non-domesticated mammals |
| KR20200091394A (ko) * | 2017-09-27 | 2020-07-30 | 페도라 파마슈티칼스 인코포레이티드 | 디아자비시클로옥탄 유도체의 약제학적 형태 및 그의 제조방법 |
| CN111556752A (zh) * | 2017-12-28 | 2020-08-18 | 富士胶片富山化学株式会社 | 冻干制剂的制造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002748A (en) * | 1976-01-19 | 1977-01-11 | Eli Lilly And Company | Method of preparing sterile essentially amorphous cefazolin for reconstitution for parenteral administration |
| JPH07114946B2 (ja) * | 1988-10-24 | 1995-12-13 | 株式会社奈良機械製作所 | 難溶性物質の処理方法 |
| US5066647A (en) * | 1989-04-20 | 1991-11-19 | Erbamont, Inc. | Cyclophosphamide - alanine lyophilizates |
| EP0589336B1 (de) * | 1992-09-22 | 1997-01-08 | Hoechst Aktiengesellschaft | Benzoylguanidine, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Antiarrhythmika |
| JP2747967B2 (ja) * | 1993-07-23 | 1998-05-06 | 雪印乳業株式会社 | シアル酸粉末 |
| ZA949182B (en) * | 1993-12-02 | 1995-07-26 | South African Druggists Ltd | Pharmaceutical composition |
| DE4430861A1 (de) * | 1994-08-31 | 1996-03-07 | Merck Patent Gmbh | Heterocyclyl-benzoylguanidine |
| DE19529612A1 (de) * | 1995-08-11 | 1997-02-13 | Merck Patent Gmbh | Sulfonyl- oder Sulfinyl-benzoylguanidin-Derivate |
| JPH09183729A (ja) * | 1995-12-29 | 1997-07-15 | Meiji Milk Prod Co Ltd | 凍結乾燥ウラシルを含有する抗腫瘍医薬組成物 |
-
1999
- 1999-01-28 DE DE19903275A patent/DE19903275A1/de not_active Withdrawn
-
2000
- 2000-01-26 ES ES00906226T patent/ES2220404T3/es not_active Expired - Lifetime
- 2000-01-26 UA UA2001085974A patent/UA70351C2/uk unknown
- 2000-01-26 CZ CZ20012693A patent/CZ20012693A3/cs unknown
- 2000-01-26 CA CA002361237A patent/CA2361237C/en not_active Expired - Lifetime
- 2000-01-26 JP JP2000595658A patent/JP4562288B2/ja not_active Expired - Lifetime
- 2000-01-26 EP EP00906226A patent/EP1146863B1/de not_active Expired - Lifetime
- 2000-01-26 KR KR1020017009423A patent/KR20010108136A/ko not_active Application Discontinuation
- 2000-01-26 SK SK1054-2001A patent/SK10542001A3/sk unknown
- 2000-01-26 AT AT00906226T patent/ATE266387T1/de active
- 2000-01-26 RU RU2001122707/15A patent/RU2225709C2/ru active
- 2000-01-26 BR BRPI0007714A patent/BRPI0007714B8/pt not_active IP Right Cessation
- 2000-01-26 DK DK00906226T patent/DK1146863T3/da active
- 2000-01-26 PL PL00351140A patent/PL351140A1/xx unknown
- 2000-01-26 DE DE50006404T patent/DE50006404D1/de not_active Expired - Lifetime
- 2000-01-26 PT PT00906226T patent/PT1146863E/pt unknown
- 2000-01-26 AU AU27986/00A patent/AU757781B2/en not_active Expired
- 2000-01-26 HU HU0105493A patent/HU226585B1/hu not_active IP Right Cessation
- 2000-01-26 WO PCT/EP2000/000569 patent/WO2000044354A1/de active IP Right Grant
- 2000-01-26 US US09/889,930 patent/US6770678B1/en not_active Expired - Lifetime
-
2001
- 2001-07-27 NO NO20013703A patent/NO331321B1/no not_active IP Right Cessation
- 2001-08-27 ZA ZA200107081A patent/ZA200107081B/xx unknown
-
2010
- 2010-06-02 JP JP2010126408A patent/JP2010264249A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO20013703D0 (no) | 2001-07-27 |
| NO20013703L (no) | 2001-07-27 |
| DK1146863T3 (da) | 2004-08-30 |
| AU757781B2 (en) | 2003-03-06 |
| EP1146863A1 (de) | 2001-10-24 |
| BRPI0007714B8 (pt) | 2021-05-25 |
| WO2000044354A1 (de) | 2000-08-03 |
| AU2798600A (en) | 2000-08-18 |
| HUP0105493A2 (en) | 2002-06-29 |
| DE50006404D1 (de) | 2004-06-17 |
| HU226585B1 (en) | 2009-04-28 |
| HUP0105493A3 (en) | 2006-07-28 |
| ZA200107081B (en) | 2003-02-26 |
| CZ20012693A3 (cs) | 2002-01-16 |
| CA2361237C (en) | 2008-07-15 |
| PT1146863E (pt) | 2004-10-29 |
| RU2225709C2 (ru) | 2004-03-20 |
| PL351140A1 (en) | 2003-03-24 |
| KR20010108136A (ko) | 2001-12-07 |
| ATE266387T1 (de) | 2004-05-15 |
| DE19903275A1 (de) | 2000-08-03 |
| JP2002535089A (ja) | 2002-10-22 |
| ES2220404T3 (es) | 2004-12-16 |
| EP1146863B1 (de) | 2004-05-12 |
| UA70351C2 (en) | 2004-10-15 |
| CA2361237A1 (en) | 2000-08-03 |
| BR0007714B1 (pt) | 2014-09-30 |
| JP4562288B2 (ja) | 2010-10-13 |
| US6770678B1 (en) | 2004-08-03 |
| BR0007714A (pt) | 2001-11-27 |
| SK10542001A3 (sk) | 2002-01-07 |
| JP2010264249A (ja) | 2010-11-25 |
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